[SomethingClever]

With regard to actual net worth, I'm probably the least successful person to post a story. But I feel I'm pretty successful in life, and I've taken a different approach than most people here. (Note: I just read through this post and it's way TLDR so proceed with caution)

It took me a year or two of college to determine that I didn't like business, economics, psychology, law or academia. What did I like? Books, movies, TV shows, magazines, advertising, etc.

As a junior I decided to major in English with an emphasis on creative writing. Everybody asked me what I would do when I graduated, with most assuming I would become a teacher. I didn't know what I would do, but I was pretty sure I wouldn't become a teacher.

This was in the late 90s, just around the time of the internet boom. My mom had gotten a job writing for a fledgling company that seemed pretty cool: Citysearch. I used that connection to get a summer job doing peon editorial work between my junior and senior year. It wasn't super exciting, but I got my fair share of fun projects, including reviewing a Beastie Boys concert and writing a multi-page feature about the 80s retro craze that was just starting to pick up.

Flash forward a year; I was about to graduate and I was hoping to find a job in Seattle rather than move back home to Portland. Boom: Seattle Citysearch was about to launch. I started out as a temporary hire with one other editor in the back room of a tiny little office in a high-rise. From there we hired an editor-in-chief and eventually grew the editorial team to about 10 writers. We also moved to a permanent location across the street from the Kingdome. I became Managing Editor in my second year there, just under the Editor in Chief. I was 23 or 24, I was making what I considered decent money to write headlines and manage the sports and movies section of our site and I had a window seat right across from the Kingdome. Here's how close it was: When they eventually demolished the Dome, the explosion cracked my window.

Eventually, after having expanded pretty rapidly, Citysearch began to contract a little. They hadn't figured out how to make enough money yet, so some of the less highly trafficked sites began losing editors and salespeople. Luckily the Seattle site was pretty huge and we were doing well, but I heard whispers that the future was down in the Home Office in Pasadena, CA.

Indeed, several jobs opened up down there, including assistant movie editor for the entire network. I applied for that and another position and was offered both. The movies job paid slightly less, but it sounded much more fun and I found out I would be working with my former Editor in Chief (who had moved down to the Home Office several months prior).

It wasn't an easy decision to move from Seattle to Pasadena due to girl-related factors (long story, not the thread for that), but I finally bit the bullet and took the job. It turned out to be the right decision and it's not close.

My job as the movies editor started with me mostly assigning movie reviews to local freelance writers and then editing their copy, but as time went on, I began writing more and more reviews myself. I started to get a little disgruntled with my boss, however, and his heavy-handed editing style of my reviews.

We had worked together for a few years and I had learned a lot from him, but at that point it felt like he was forcing his voice on my reviews. Just when it was getting pretty annoying, he took another job and moved back to Seattle. We were still on good terms, and he was ultimately a great guy to have worked for.

But now, I was running the entire movies department by myself! I assigned all the reviews, choosing whichever I felt like reviewing myself. It was a pretty sweet gig... I reviewed anywhere from 1-3 movies a week and spent the rest of the time editing and writing headlines.

Eventually, however, contraction reared its ugly head again. The company still wasn't profitable, despite scaling back in a pretty big way. There were rounds of layoffs, mostly affecting the local city staff and not the Home Office.

A side effect of the contraction was that editorial was constantly being forced to re-examine how we were writing content. We eventually were forced into writing extremely short-form copy, because the general consensus was that people didn't like reading long copy on the internet (lol). The aim of all this was to make the site profitable. We kept changing the way we reviewed restaurants. At one point we were in a meeting with the new CEO (or something, I can't remember his title) and he told us point blank that we were no longer in the business of writing negative restaurant reviews. Of course all the editors threw a [censored] fit, but corporate's defense was that the site was supposed to help people find the great things in their city, so we could "edit out" the places we didn't like and it wouldn't make any difference.

I was getting pretty jaded and I told them that the whole thing sounded like a slippery slope, but I was ignored. A few months later, I was laid off. I think it was the 5th or 6th round of company-wide layoffs, so I had survived a lot longer than most. The Seattle and Portland offices had been totally decimated, for example.

It was actually kind of a relief when I found out. I had gotten a flat tire that morning and was at home when they called me. I remember laughing when I heard. I wasn't disappointed at all... I actually felt free.

See, at that point my plan was only to stay at the job for another 6 months or so, then go traveling with my wife (we had gotten married a few months prior), then move to Portland.

We weren't quite ready to go travling yet, but it seemed like a good time to move back to Portland, so we adjusted our plans a little. We'd move back north, I'd get a job and work for a year or two, then we'd travel.

Well, we moved, but getting a job in Portland proved tougher than I thought. I had been saving for a house and I also got some severance from CS having worked there for 5 years, so I had plenty of money, but I just couldn't land a job... let alone an interview.

It was around this time that I discovered online poker, by the way (late 2003). My brother and brother-in-law (pizownored and balkii) were making money at it, I had lots of time on my hands and money, so I gave it a shot with $50. I built that up into $350 or so playing $25 NL like a complete fish, then slowly lost it all. This experience turned me into the nit I am today. I HATED losing that money, even though it didn't mean much to me. I would play late into the night, grinding away, slowly losing due to my horrible play and then go to sleep absolutely PISSED at myself.

I read Theory of Poker, threw in another $50 and lost it. I started 4-tabling play money SNGs (OMFG) while I looked for jobs during the day. Eventually I played a little 25NL on pizownored's account, won $11 and entered a $10+1 SNG. I won, and had him transfer me the $50.

This time I sort of knew what I was doing, and built that into $550. But I had a "major" downswing and lost that down to $300 and decided to cash it out.

Side note: I wish I hadn't had the initial horrible experience of losing all my money as a fish. Because ever since then I have panicked and cashed out rather than moving up. I've never been able to cultivate the fearlessness and gamble that you need to succeed at higher levels, and so I've always been a low-stakes grinder. I make a decent side income from poker, but I wish I had moved up more aggressively back in the day.

Meanwhile, I got a job as an advertising copywriter. Funnily enough, it was the first job I had applied for, back in December while still living in LA. They had just taken 5 months to get their act together and start interviewing people. There were 180 applicants, and they interviewed anyone who sent in writing samples.

This was in 2004 and the housing market was really heating up in Portland. Luckily I had the down payment just sitting in the bank... all I needed was a job and my wife and I could start house hunting.

It was a crazy time to buy a house. Everything sold on the first day, usually for more than the seller was asking. We made 2 offers on other homes before getting our third accepted. We paid about $10,000 over asking, and we still only got the place because a friend of my wife's family knew the sellers.

Flash forward 3 years to today. My wife is almost done with her graduate program and I'm about ready to leave work. We're going to sell or rent our house (it has appreciated nicely) and go traveling for 6-12 months.

I'm extremely burned out on advertising after only 3 years, and I don't know what I'll do when we get back, but we have a nice little cushion thanks to poker and the appreciation on our house, so I don't have to worry about it yet.

I also don't feel like I need a ton of money to get by. I already own almost everything I could want (notable exception: Triumph Bonneville T100, which I'm waiting to purchase until we get back).

I've been half-heartedly working on a book for the past couple years that I think has pretty decent potential for getting published. I hope to finish it while traveling... and we'll see what happens when we get back.

The best advice I can offer is to really take stock of what makes you happy. For me, it's not money. I'm sure I could have gone into business or law or another well-compensated field and made tons more money than I did. But I did just fine. And now that I'm sick of my current job, I will be moving on (if it weren't for the trip, I probably would have already left).

I feel sorry for people who drive an hour into work from the suburbs in their nice car, work long hours to afford the nice car, then fight the traffic back home again. Not the life for me.